(3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

Base Information

• Chemical Name: (3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine
• CAS No.: 141063-01-6
• Molecular Formula: C₅₆H₆₂N₇O₈P
• Molecular Weight: 992.124

Synonyms:(3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

Chemical Property of (3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of (3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine

There total 12 articles about (3S,4R)-N⁶-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + (3S,4R)-N6-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine → (3S,4R)-N6-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (141063-01-6)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00038a037

Reference yield:

3,4-Dihydrophenanthrene (56179-83-0) → (3S,4R)-N6-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (141063-01-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 75 percent / OsO₄, pyridine / 4 h / Ambient temperature

2: benzoic acid / benzene / 3 h / Heating

3: Et₃N, Me₃SiCl / CH₂Cl₂ / 3 h / 4 °C

4: NaN₃ / dimethylformamide / 60 °C

5: 93 percent / NaOMe / tetrahydrofuran; methanol / 2 h / Ambient temperature

6: 74 percent / H₂ / 5percent Pd/C / methanol / 4 h / Ambient temperature

7: 13 mg / hexamethyldisiloxane, 2,6-lutidine / dimethylformamide / 4 h / 90 °C

8: 81 percent / pyridine / Ambient temperature

9: 88 percent / n-Bu₄N⁺F^- / tetrahydrofuran / Ambient temperature

10: 69 percent / Li₂CO₃, 2,6-lutidine / 1.) r.t., 3 h, 2.) 0 deg C to r.t., 15-20 min

11: 62 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; sodium azide; Hexamethyldisiloxane; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; lithium carbonate; triethylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00038a037

Reference yield:

(+/-)-1,2,3,4-tetrahydro-4-phenanthrenol (56179-82-9) → (3S,4R)-N6-(4-(3-acetoxy-1,2,3,4-tetrahydrophenanthrenyl))-5'-O-(4,4'-dimethoxytrityl)-3'-O-<(N,N-diisopropylamino)(β-cyanoethoxy)phosphinyl>-2'-deoxyadenosine (141063-01-6)

Guidance literature:

Multi-step reaction with 12 steps

1: p-toluenesulfonic acid / benzene / 45 h / Heating

2: 75 percent / OsO₄, pyridine / 4 h / Ambient temperature

3: benzoic acid / benzene / 3 h / Heating

4: Et₃N, Me₃SiCl / CH₂Cl₂ / 3 h / 4 °C

5: NaN₃ / dimethylformamide / 60 °C

6: 93 percent / NaOMe / tetrahydrofuran; methanol / 2 h / Ambient temperature

7: 74 percent / H₂ / 5percent Pd/C / methanol / 4 h / Ambient temperature

8: 13 mg / hexamethyldisiloxane, 2,6-lutidine / dimethylformamide / 4 h / 90 °C

9: 81 percent / pyridine / Ambient temperature

10: 88 percent / n-Bu₄N⁺F^- / tetrahydrofuran / Ambient temperature

11: 69 percent / Li₂CO₃, 2,6-lutidine / 1.) r.t., 3 h, 2.) 0 deg C to r.t., 15-20 min

12: 62 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; sodium azide; Hexamethyldisiloxane; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; lithium carbonate; toluene-4-sulfonic acid; triethylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00038a037

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

3,4-Dihydrophenanthrene

(+/-)-1,2,3,4-tetrahydro-4-phenanthrenol

(+/-)-cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene

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